


One Last Night

by orphan_account



Category: Supernatural
Genre: Alternate Universe, Angst with a Happy Ending, Depressed Dean, Emotional Hurt/Comfort, First Kiss, Implied/Referenced Suicide, M/M, No Sex, Past Rape/Non-con, Past Suicide, Poor Dean, Pre-Relationship, Prostitute Sam, Suicidal Dean, Suicidal Thoughts, Unrelated Dean Winchester/Sam Winchester
Language: English
Status: Completed
Published: 2016-06-10
Updated: 2016-06-10
Packaged: 2018-07-14 05:28:11
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 6,278
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7155548
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Dean Winchester has a miserable life. He's poor, he has no friends, no family, and no real reason to live. He decides he's going to end it all, but wants to spend his last night alive doing something more than sitting alone. So he takes the last of his money and hires a kind hooker to stay the night and talk with him.</p>
            </blockquote>





	One Last Night

**Author's Note:**

> This was written based on a prompt given from the Daily SPN Prompts page on Tumblr. The original prompt was: Poor!Dean is lonely and spends his remaining cash for the week on a prostitute, not to sleep with but to just sleep with ‘cause he’s feeling down in the dumps. 
> 
> [Link to the Original Prompt here.](http://dailyspnprompts.tumblr.com/post/144716373779/t-dean-x-unknown-oneshot)
> 
> [Link to DailySPNPrompts Blog Here](http://dailyspnprompts.tumblr.com/)

Dean Winchester had no friends. He had no family. He had two hundred dollars to his name for the entire month, unless he found a better paying job, which, in this economy, was highly unlikely.

 

When Dean had turned eighteen he was sure he would be a hero. He had the biggest dreams in the world. He wanted to be a writer, or a doctor, or maybe a scientist. But he had one major problem… He was a straight D average student and pretty much every college laughed him directly out of their admissions program.

 

He finally got into a crappy community college and managed to scrape by in his classes long enough to get a bachelor’s degree in English. Of course, no one had been around to tell him that an English degree without the motivation and the ability to work for zilch was worthless.

 

In addition to his degree, he’d racked up a substantial debt with student loans that he couldn’t pay off without a good job. Which he couldn’t get.

 

So Dean stuck with his part time fast food jobs, let the collectors call, and used his degree for toilet paper; that was all it was really worth anyway.

 

Dean sat in his messy, roach infested one-bedroom apartment - with a toilet that clogged every other day - on his threadbare, sagging couch from the seventies, and wanted to cry.

 

He had nothing. No one would miss him, no one would care. Honestly, if he turned up dead, they probably wouldn’t even find his body until he started stinking bad enough for the few neighbors that weren’t crack addicts to notice.

 

But who cared? If no one cared about him, why should he care about himself?

 

Dean tried to tell this to himself as he held the handful of pills – a leftover prescription from the time he broke his leg on the job – but he was too weak to take them.

 

He tried to tell himself this as he held the knife to his throat – but he couldn’t make the cut.

 

He rose from the couch with some effort and padded into his kitchen. Two plates, one chipped coffee mug – but no coffee machine – a single frying pan and pot, and a single fork, knife, spoon, and cutting knife were all he boasted for housewares.

 

Dean opened his fridge, sighing. A moldy sandwich from work, a half bottle of ketchup, and a pack of month old eggs stared him in the face. A six pack of beer was sitting on the counter next to the four packs of ramen he would be eating for the remainder of his time alive.

 

He’d paid his rent this month, two hundred dollars, and his lights, another hundred, so at least he’d have a place for his body to rot.

 

Grabbing one of the beers, Dean cracked it open and sat back on his couch, digging around in the cushions for spare change. He’d had a phone, but the bill got to be too expensive. He’d also had a car at one point, but had to sell it when he’d broken his leg to pay for his hospital bill.

 

The streets weren’t dangerous, not really, not if you knew where to walk. But knowing where to walk also meant knowing exactly _what_ was on each street, including where all the hookers hung out.

 

Blanchard Avenue was hooking central. Gay boys, studs, females, even transsexuals and senior prostitutes hung out in the houses and on the lawns of this street.

 

This was exactly where Dean was at ten in the night on the last night he planned to be alive. He was wandering down the street, not really looking at anyone. His hands were stuffed in his pockets, his left lightly fingering the sheaf of bills – every penny he had.

 

“Hey guy, you looking for someone?” A young male voice sounded from his right. Dean stopped, looking for the source of the voice.

 

An extremely tall man stepped from the shadows. Even in the low light, his beauty took Dean’s breath away. Shaggy hair and floppy bangs made him look much younger than he probably was. He was thick, muscles everywhere from what Dean could see – which was quite a bit considering the man was wearing a tight white tank top that cut off halfway down his belly and a pair of ripped denim shorts that barely covered his bulge and peeked a tuft of pubic hair from the top. He was wearing flip-flops, allowing the full view of long, tanned legs.

 

“No, but you’ll do. How much?” Dean asked, trying to sound confident, but sure he came off as awkward; he always came off as awkward.

 

The man smiled, a stunning smile that showed a line of beautiful white teeth. His tongue darted out of his mouth, wetting his cocksucking lips.

 

“But I don’t know if you’ll do. What’re you lookin’ for, sweetheart?”

 

“I uh—I – I w- I want someone to sleep with,” Dean stuttered.

 

The man laughed. “That’s what everyone in this area wants, guy. What’re the particulars?”

 

“W—What do you mean?”

 

The man’s brows furrowed. “Okay, you haven’t done this before. Tell me what you want to do. Do you wanna get fucked? Or wanna fuck me? I’ve got a great ass for fucking, if you’re curious, but I won’t go bareback. You want a blowjob? A handjob? Everything’s got its own price.”

 

Dean stumbled over his words, face reddening, “No! No, I don’t want -- I don’t want any of that. I just want – I want someone to sleep with me tonight.”

 

“So just basic sex?” The man asked, clearly confused.

 

“No, no sex. I just want someone to spend the night with me. I—I wanna pay you to come to my house and just… Hang out with me.” He looked at his feet, staring at his scuffed logging boots, turned inward with his bowed legs. This was a bad idea. He sounded like an idiot. “I—I’m sorry, this was a bad idea.” He turned to go, but the man grabbed his shoulder.

 

“Wait, man. Look, I’m a hooker. I need to make money. How much are you willing to pay for me to come and hang out with you?”

 

“I—I only have two hundred. I’ll give you it all.” Dean said, knowing he sounded much too eager as he looked at the young man with the beautiful smile.

 

“Alright, two hundred is fine. But if you want anything else, it’ll cost you more, okay?”

 

“Yes, of course.”

 

“Alright. And I need your address to give to my friend, so he knows where to pick me up tomorrow. It’s a safety thing.”

 

“O—Of course.” Dean stumbled through his address, heart in his throat. He was really doing this.

 

The man left, returning shortly. “Great, we’re good to go. Where’s your car?”

 

“I—I don’t have one. I walked.” Dean whispered, shame overriding his excitement once more.

 

“Oh. Well no problem, it’s not far. Let’s go.” The man set his hand on Dean’s lower back, guiding him back the way he came.

 

They walked in silence for a long time, until the man finally spoke up,

 

“So what’s your name?”

 

“Uh, Dean. What’s yours?”

 

“Sam.”

 

“Hi, Sam. I—I know this is probably weird for you.” Sam laughed loudly,

 

“That’s an understatement. But it’s okay, man. Everyone has different needs. Honestly, it’ll be nice to not get fucked by some smelly john tonight.”

 

Dean tried to laugh, but it came out choked and forced, ending their conversation once more.

 

Dean hesitated at his front door. “Listen, uh… My place, it’s really nasty. Like, I keep it clean but the apartment in general is just a bad place, so… I’m sorry.” He mumbled.

 

“No worries, I’ve probably been in worse,” Sam said, shrugging.

 

Dean nodded and unlocked the door, pushing it open and walking in. He sat down on his couch and pulled his shoes off, pulling out the money and setting it on the chipped and scratched coffee table. “There’s your money.”

 

“Thanks,” Sam grabbed it and pushed it into his pocket, looking around the apartment. “It’s not too bad.”

 

“It’s pretty bad,” Dean argued. “Want a beer?”

  
“Sure. I’ll grab it, you want one?” Sam offered, and walked into the kitchen.

 

“Yeah,” Dean called, watching the gorgeous man walk through his pathetic excuse for a home.

 

He could see Sam from the doorway, so when Sam opened the door and stared, shocked, at the nearly empty fridge, there was no mistaking it.

 

He returned with the beers and sat next to Dean slowly, the couch groaning warningly with the extra weight.

 

“Can I ask you a question, Dean?”

 

“Sure. I mean, I’m paying you to hang out, so I guess, um – Talking is supposed to happen.”

 

Sam was silent for a moment, picking at the beer label. He took a long drink and set the bottle down. “Why are you spending money on a hooker when you don’t have any food in your house?”

 

Dean looked down at his own beer, “I really don’t wanna talk about it.”

 

“Okay… Just, it doesn’t make sense to me, sorry. So what do you wanna talk about?”

 

“Um, I don’t know. What do people talk about when they hang out?” Dean could feel Sam staring at him. A glance over proved it.

 

“I guess--” Sam shrugged when Dean met his gaze, “I normally talk about my work or my favorite sports teams or tv shows.” He looked around the apartment. “So what teams do you like?”

 

“I don’t watch sports. I don’t have a tv.” Dean said weakly. “I um, I sold it about a year ago. I broke my leg at work and had to pay for the hospital bill.”

 

“Why didn’t worker’s comp cover it?”

 

“My boss threatened to fire me if I filed worker’s comp. I couldn’t lose my job,” Dean shrugged.

 

“Well, what do you do for a living?” Sam tried again to start a conversation.

 

“Oh, I work at Biggerson’s. I’m a bus boy.”

 

“Well that’s not too bad of a job,” Sam tried, and Dean smiled weakly.

 

“It’s crap, honestly. Long hours and barely minimum wage.”

 

They sat in silence for a while, conversation not working very well.

 

“Do you have a deck of cards?” Sam finally asked about ten minutes later.

 

“No, sorry.”

 

“Well what do you do when you’re not working?”

 

“Usually at the library looking for another job. Sometimes I can pick up odd jobs around town fixing things or mowing lawns – but most people prefer teenagers for that kind of stuff,” Dean explained.

 

Sam shifted on the couch so he was facing Dean, his legs curled underneath him.

 

“Listen, man, I know it’s none of my business, but… You’re a super handsome guy, you seem pretty well educated. Why are you living like this? What’s your backstory?”

 

“My—My backstory?”

 

“Yeah, your life. I’m curious. You tell me yours and I’ll tell you mine.”

 

“Is that something people do normally?”

 

“You act like you’ve never had a new friend,” Sam joked. When Dean looked at him, eyes watery and hollow, Sam’s face dropped.

 

“You don’t have friends, do you?”

 

Dean shook his head slowly.

 

“Oh. Wow. Um, okay, yeah, that’s what new friends usually do. So spill, Dean.” He offered a comforting smile that came off as pitying.

 

“Well, where should I start?” Dean asked softly, turning to face Sam as well.

 

“The beginning.”

 

“Well, I was born to John and Mary Winchester… Um, I had a little brother, he was f—four years younger than me. His name was Sam too. We were good but um—My—my mother was killed, murdered in an arson fire wh—when I was four. My little brother too.”

 

Sam’s eyebrows shot up. “Holy shit, I’m so sorry, Dean.” Dean blushed a little and shrugged. “Long time ago.”

 

“How old are you?”

 

“Thirty-two.” Sam nodded,

 

“I’m twenty-eight. Sorry, I distracted you, please, continue.” He took a sip of his beer and sat back as Dean began to speak.

 

It was difficult to talk so much to another person, Dean realized, but his voice became smoother, his stuttering less frequent, as he delved further into the story.

 

“So my dad was left with me, but I was four and kind of messed up after the fire. He um, he kinda lost it and got committed… I’m not sure if he’s alive even to this day.

 

But anyway, my gramma took me in, but she was too sick to really take care of a kid, so I spent most of my childhood taking care of her. When I was fourteen I got my first job to try and help us pay bills – her disability pay was kinda shit.”

 

Dean hesitated, taking a long swill from his bottle. He took the moment to notice Sam then, the way his expression was softened; he was really listening to Dean. It was a strange feeling, knowing someone was actually paying attention when he spoke, but it was a nice feeling.

  
After a moment, he swallowed hard and began speaking again, “So I worked all through highschool, sometimes I skipped classes to work, because I had to go home and take care of my grandmother too. Course, because I was focused on work and my gramma, my grades dropped. I barely graduated, so no college would really accept me. I decided to keep working and helping her pay her bills instead.

 

Once my gramma died, I was nineteen, by the way, I decided to try school again. I got into the local community college and graduated after four years, but it was pointless.”

 

“Why?” Sam asked, leaning forward intently by this point.

 

“Because I majored in English. There’s really no jobs around here for English majors, and I can’t afford to move anywhere.”

 

Sam nodded, his face softening a little more in sympathy – _sympathy_ , not pity – Dean noted.

 

“What did you want to be originally?” Was Sam’s next question.

 

“I wanted to be a writer, actually. Fiction stuff. I love books, even though my grades don’t show it. I’ve always wanted to write books for teens.”

 

“That’s awesome, Dean. Why don’t you? I mean, you could work and still write.”

 

Dean shrugged, running his thumbnail under the label of the bottle. “I don’t really have the urge anymore. Kinda fucked up, to be honest.”

 

Sam reached out, setting his hand on Dean’s knee. He rubbed gently, smiling softly. “It’s okay. Keep going, I’m really interested.”

  
“Alright, well, once I graduated, I realized my degree was useless, but I’d racked up like a hundred thousand dollars in student loans. I mean, I’m never gonna pay that off, you know? Especially because I’m still working in fast food.

 

I can’t get a better job, because I have a useless degree, and even if someone wants someone with a degree like mine, my grades were crap because I hadn’t paid enough attention in school, so they won’t take me.

 

So here I am. In my shit apartment with no friends because I never learned how to really talk to people, no family alive, and with my crappy job and two hundred dollars left to my name for the rest of the month, talking to a prostitute that I asked to come home because I was lonely and didn’t want to spend my last night all alone.”

 

Sam scowled when Dean finished. He’d removed his hand from his knee while he was talking, but now set it back firmly, squeezing gently.

 

“What do you mean your last night?”

 

Dean chewed his lip, hesitant to answer. Telling a life story was one thing, but telling plans like this—

 

“I’m gonna kill myself tomorrow. Not that you care, sorry. I just know things aren’t worth living. So I figured I should enjoy my last night.” Dean offered a smile he hoped was comforting, but Sam didn’t look convinced.

 

“That’s why you’re giving up the last of your money. And why you have no food in the house.”

  
Dean nodded, looking away from Sam. “Sorry, that was out of line for me to share, wasn’t it?”

 

“No.” Sam moved his hand to Dean’s wrist, rubbing his thumb over the pulse point. “I’m actually really glad you told me.”

  
“Why?”

  
“Remember when I said if told me your story, I’d tell you mine?”

 

Dean nodded.

 

“Well, my story might be helpful to you – I think it’ll be really helpful to you, now that I know.”

 

Dean worried his lip between his teeth once more. “Well, alright, what’s your story?”

  
Sam looked around the shabby apartment. “Where’s your bedroom? Let’s order a pizza and lay down in bed to talk.”

 

“I can’t – I don’t have money remember?” Dean asked, his brows furrowed.

 

Sam dug in his shorts pocket and pulled out the fold of twenties Dean had given him earlier. He counted out a hundred and eighty of it and pushed it into Dean’s palm. “Now you have money for pizza. Come on, I’m starving. It’s customary to feed your friends when they come visit.”

 

“I—I have no phone.” Dean admitted, looking down in shame. He tried to push the money back at Sam, but Sam pushed back.

 

“I do.” He pulled a cell phone from his pocket and opened it. “What do you like on your pizza?”

 

The two sat in silence on the couch until the pizza arrived, neither really knowing what to say at the moment. Dean rose when the knock sounded at the door, looking guiltily at the money Sam had handed him. “Are you sure about this?”

 

“Of course. Two hundred for a night of talking is kind of ridiculous.”

 

Dean smiled a little and answered the door, paying the man and returning to the couch with the stack of pizza and breadstick boxes. “It only came to forty. Here.” He tried to hand Sam back the money.

 

“Just set it on the table,” Sam said, rising and taking half the boxes.

 

Dean did as he said and led Sam into the bedroom, just as shabby as the rest of his house. He had a queen sized bed at least, though the mattress was sagging in the middle, and most of his pillows were flat.

 

Sam seemed to pay no attention to any of this however, simply climbed onto the bed and spread out the pizza boxes, opening one and pulling out a large slice of veggie only.

 

Dean sat next to him, taking a breadstick and nibbling at it. His stomach was growling, hunger getting the best of him with all this food in front of him, but he couldn’t bring himself to eat something he hadn’t earned.

 

Sam leaned back on the bed and crisscrossed his legs. “So, you wanna hear my story?”

 

“Yeah, of course.” Dean looked at him with a rapt expression on his face that made Sam smile.

 

“Alright, I guess here goes nothing. I don’t talk to many people about my childhood and stuff, so forgive me if I sound a little nervous.”

  
Dean nodded, eager to listen to Sam talk – he had such a pretty voice.

 

“I was born to a really good family, my mom and dad were the best, gave me everything I ever wanted. I mean, to say we were rich would be the understatement of the century.”

 

Dean shook his head, making Sam pause.

 

“Wait, if you’re so rich, how’d you get into hooking?” He asked, and Sam smiled weakly, shrugging.

 

“Oh, how the mighty have fallen,” He said, then clarified, “You’ll understand when I tell more.”

  
Dean frowned but conceded, giving a nod for Sam to continue.

 

“So anyway, things were great until I was about fourteen. See, my dad made so much money because he was a hedge fund manager. I don’t know if you know much about what they do, but they make crazy money if they’re good at their job. Which is what I thought my dad was… But it turns out he was actually working a fraudulent scheme, he’d take money out of people’s accounts by saying they were investing in different things, but he’d put it in his own account instead.

 

So the FBI found out and caught him. We lost everything and he went to jail. When I say everything, I mean _everything_. Our house, all of our cars, our land, everything. Me and my mom had to move into this crappy little one-bedroom apartment, actually not too far from here.”

 

“Is she still alive?” Dean wondered aloud. Sam’s expression darkened a little. He gave a barely visible shake of his head, picking up another piece of pizza.

 

“No, I’ll get to that though.” He frowned when he saw Dean still working on the first breadstick he’d picked up. “Dude, eat. It’s not like we’re gonna run out of food. We got six pizzas and three orders of breadsticks.”

 

Dean flushed red and nodded, picking up a piece of pepperoni pizza. He stared at it like it was foreign before taking a small bite and looking at Sam as he chewed.

 

Sam grinned from ear to ear. “See? Not gonna kill you. Anyway, I’ll get back to my story.

 

So my mom had never worked a day in her married life. She hadn’t had to, so when she went back into the job market she pretty much had no relevant experience. It was impossible to find work. She got a crappy job at a grocery store, but it was barely enough to cover our rent. Most of the time we’d go without eating for days.”

 

Dean looked guiltily at the food on the bed in front of them until Sam reached over and touched his leg. “It’s cool, Dean. I promise, you’re not taking food out of my mouth – I make nearly a grand on a good night.”

 

“A night?” Dean squeaked, clearly shocked.

 

“Mhm. Boys pay a lot of money for this body.” He wiggled on the bed playfully, and Dean had to smile, laughing a little.

 

“So anyway, she was working while I went to school, but I felt so bad, you know? I hated seeing her work so much while I just got to hang out with friends and do sports. So I found other ways to make money.

 

I started selling pot first. You have no idea how many rich kids like getting high with their parents’ money, so it was a pretty good job… But there was a lot of competition. It was hard to get a foot in that market, even if you had friends.

 

One thing led to another, and I ended up in one of my teacher’s houses one night. I was sixteen, and he found out I’d been selling weed in his classroom. He made me come to school for detention and offered me a bottle of water. I didn’t know it at the time, but he’d slipped a drug into it. While I was knocked out, he brought me to his place and tied me up. Raped me.”

 

Dean felt the little bit of food he’d eaten rise back up his throat at the mention of rape. He reached out instinctively, brushing Sam’s hair behind his ear and setting a comforting hand on his neck.

 

Sam smiled a little, leaning into the touch. He snaked his own hand up, setting it over Dean’s, his eyes closed. He began speaking again, softer and slower, still not opening his eyes or moving away from Dean’s touch.

 

“He uh, he wasn’t very nice about it, if you know what I mean. I’m still sure I shoulda gone to the hospital with what he did, but I didn’t.”

 

“Were you scared? That he’d hurt you again if you did?”

 

“No, God no, that wasn’t it.” Sam opened his eyes as he spoke. He kept his hand on Dean’s though.

 

“Honestly, it was because I wanted to forget it happened. I was a virgin before it, I mean, I’d sucked a few dicks and made out with some guys, but I was really big on saving myself for the right guy, you know? So when he did that, I just… I felt dirty, like I’d been ruined and I was worthless.”

 

“You’re not worthless, Sam. I mean, a worthless person wouldn’t be here right now.”

 

Sam smiled sadly, but ignored the compliment. Instead, he continued his story,

 

“What really shocked me though, wasn’t so much that I’d been raped. It was that he left me on my doorstep with five hundred dollars stuffed into my jeans pocket. That’s what made me realize being a hooker might be the way to go to, you know, save my mom from working herself to death. So that’s what I started doing.

 

I worked on weekends originally, I didn’t want to quit school and I couldn’t let my mom know what I was doing, I mean she didn’t even know I was selling pot. So I just earned the money when I could and started leaving it around the house. A couple of extra twenties in her pocket or slipped into the couch or dropped randomly on the floor.

 

She didn’t notice at first, for a year or so, actually, but it started getting fishy for her when she realized our bills were all caught up and we still had money to spend on food. She confronted me about it.

 

I uh, I told her the truth. Me and my mom had gotten super close with my dad in prison, so I knew it wouldn’t be fair to lie to her about it. I was enjoying the money and I loved seeing her be able to get new things and live, even a little bit, how we used to…

 

She told me that she wouldn’t have me doing anything like that under roof. My options were to quit or get out.”

 

“What did you do?” Dean asked. He’d let his hand drop from Sam’s face but kept it on Sam’s leg, rubbing gently. Sam shrugged, taking a bite of food.

 

“I quit for a while. But we started falling behind again almost immediately. Bills adding up, our water and lights getting shut off… So I went back to hooking. Instead of hiding it or doing it sneakily, I walked up to her after one weekend and handed her fifteen hundred dollars. She knew where it was from immediately. She uh, she threw it in my face and told me to get out. Three days later she was dead. She’d slit her wrists in the tub.

 

Left a suicide note about how her husband had lied to her and son had lied to her and she was all alone in life… But had she--” Sam’s voice broke and he hung his head.

 

“If she’d just let me in, let me stay regardless, I—I could’ve helped her.” He looked up at Dean slowly, his bright eyes wet with unshed tears. “I’ve been hooking ever since.”

 

Dean didn’t hesitate after Sam’s final sentence. He pounced, landing in Sam’s big lap and wrapping his arms around him in a desperate hug, nose buried in the crook of Sam’s neck.

 

He felt the tears soaking his shirt, Sam’s big hands fisting the back of it and twisting. So this was what a true connection with a person felt like. It hurt, but it felt good, so good, in a way he’d missed without even knowing what it was.

  
Dean gripped Sam tighter, reaching one hand up to stroke through his shaggy hair. They’d both had shitty lives, both had reasons to hate and to be depressed. They both needed the touch of someone real. A touch that meant something.

 

When Sam’s tears finally dried to sniffles, Dean loosened his grip on Sam, moving off his lap, He smiled nervously, reaching out to wipe the tear tracks on that beautiful face.

 

“Sorry if that was out of line, I just—“

 

“No, god. Don’t apologize,” Sam whispered, “That’s… Probably the best response I’ve ever gotten. It was really nice, Dean.”

 

Sam’s expression changed then, confusing Dean. He leaned forward slowly, reaching out to touch Dean’s face. It looked like he was going to – oh no.

 

Dean pressed his palm flat to Sam’s chest, stopping him inches before Sam kissed him. “Hey, that’s not a good idea,” He said softly.

 

Sam leaned back, then frowned. “Oh god, you’re not gay are you?”

 

“What? No, I am definitely gay,” Dean said, laughing a little.

 

“So then… What’s wrong?”

 

Dean looked away, his cheeks burning hotly. “I um… I haven’t actually ever, _done_ … Anything. And.. I don’t have more money for you and I know you said anything more than talking would be more and –“

 

“Wait, you haven’t done _anything_?”

 

“Nope.”

 

“You’re a virgin? Not even a girl?”

 

Dean shrugged, the heat in his cheeks increasing. “Nope.”

 

“No blowjobs or handjobs or… Anything?”

 

“I—I haven’t even kissed anyone, Sam.”

 

Sam leaned back, his shoulders slumped. “Shit, I am so sorry, Dean. I—I didn’t have any idea. I mean, you’re so damn cute, I just assumed you’d been with people. God, I know you don’t want your first – anything to be with a hooker, I am—Can we pretend that didn’t happen?”

 

It was Dean’s turn to scowl, confused. “Wait, you think I won’t kiss you because you’re a hooker?”

 

“Well, yeah. I mean, I wouldn’t want my first kiss to be some street urchin.”

 

Dean laughed, loud, and Sam jumped. He covered his mouth, his eyes wide. “Sam, that’s not it at all! My god, no, you’re – you’re gorgeous and, hooker or not, I would absolutely kill to have you be my first anything. But, I—One, I don’t have the money to pay you, and two, I mean, who wants to kiss a guy who’s thinking of, you know…”

 

“You’re still wanting to do it, huh?” Sam asked softly. Dean nodded slowly.

 

“I feel bad admitting that, after your story, but… It doesn’t change how I feel.”

 

“Why do you want to kill yourself, Dean? Please, just answer me that honestly.”

 

Dean scowled. It was a question he’d thought of himself, but never had to verbalize the answer to. It all made sense in his head though, so maybe it’d make sense out loud.

 

“I’m alone. I mean… I have no friends; my coworkers don’t give two shits about me. Most of them are high school kids who think I’m just a felon or a dropout. My whole family is gone. I barely make enough money to pay my rent, let alone get out of debt or save anything. I don’t have anything to live for.”

 

“So, if you, for example, had something to live for… You wouldn’t kill yourself?”

 

“Of course not,” Dean said, offering a weak, confused smile, “But what does that matter?”

 

Sam leaned forward, taking Dean’s hands in his own. He twined their fingers, waiting until Dean met his eyes.

  
“What if I gave you something to live for?”

 

“What do you mean?”

 

“I mean… I’m a hooker. I make plenty of money. I have a decent apartment. How much does this place cost?”

 

“T—Two hundred a month plus an extra hundred in utilities.”

 

“Alright. My place costs a grand. Why don’t we find a place and move in together? Not as fuck buddies or boyfriends, but just as two guys helping each other out. We can find a place in the middle, say… Three to six hundred a month. I’ll cover the rent and utilities, you cover the food and housecleaning. It’ll let you start paying off those student loans, and maybe even save up a little so you can move to a place where you can put your degree to good use. Or you could even start writing again, if you got the inspiration for it.”

 

Dean pulled his hands back, holding them up, palm out, in front of his face. “You don’t even know me.”

 

“Maybe not. But I see a guy who needs a friend. And I—I need to make things right. I screwed up a lot in my life. My mom, some friends I had that were good people before I started hooking… I know you aren’t going to kill me in my sleep, and I don’t have all that much to steal… What harm could it do?”

 

Dean looked down, biting his lip in thought. He liked the idea – loved it to be honest – but it all seemed too good to be true.

 

“Is there a catch?” He finally managed to gather the courage to ask.

 

“Of course there is.” Sam said, smiling when Dean’s head snapped up.

 

“The catch is that you have to stay alive. You have to promise me that if you’re feeling suicidal or depressed, or just want someone to talk to, or hug, or even just lay in bed with, that you’ll come to my door or you’ll call me.”

 

“Can I—“ Dean hesitated, overwhelmed, “Can I think about this?”

 

“Of course. Look, I’m getting a little sleepy. Why don’t you get into whatever you normally sleep in and I’ll put this food in the fridge.”

 

“Do you have something to sleep in? Those shorts can’t be comfortable.”

 

“Not really – no underwear means easier access.” Sam admitted as he rose from the bed and began to gather the boxes up.

 

“I have a pair of boxers that’ll probably fit you. They’ll be a little tight, but more loose than those things.”

  
“Sounds good,” Sam said before walking into the kitchen.

 

Dean watched him go then rose, padding to his dresser. He opened the top drawer and took out the prescription bottle of pills – his preferred method he’d decided. He set it on top of the dresser before pulling out a pair of boxers for Sam, then stripping into his own boxers and undershirt.

 

Sam returned shortly and smiled. “You’re handsome, you know. If you’d get over that shy thing, all the boys would love you.”

 

Dean laughed, lowering his head and rubbing the back of his neck. Sam closed the gap between them and took Dean’s shoulders in his hands. “But the shy thing is kinda cute.”

 

Dean’s breath punched out of him when he met Sam’s gaze. He’d been staring into those beautiful, color changing eyes all evening, but each time was so much more beautiful.

 

“Hey, another part of that deal could be that I’d let you kiss me for free tonight – if you wanted to, that is.”

 

“Just tonight?” Dean whispered, his gaze dropping to Sam’s damp, parted lips.

 

“Well, maybe every night, if you were living with me.”

 

Dean wrapped his arms around the back of Sam’s neck before he lost the nerve and went up on his toes, kissing Sam deeply. His heart was in his throat, and he knew Sam could probably feel him shaking all over.

 

Sam gave no inclination though, he simply wrapped his arms around Dean’s lower back and pressed their bodies together, deepening the kiss until they had to part for air.

 

Dean’s mouth twitched into a smile, taking in the sight of Sam’s mouth, swollen and red, and his cheeks, speckled with a light blush.

 

“I—“ he stepped back and grabbed the pill bottle, “This is what I was going to use. Here.” He shoved the bottle into Sam’s hands. “Flush them, do whatever you want with them.”

 

“Does that mean you’ve decided about my deal?”

 

Dean wet his lips, looking anywhere but Sam for a long time after that question was posed. It hung heavy in the air for him – a huge step that he would have to take alone.

  
But, he wasn’t alone. His eyes finally met Sam’s again and he saw something he’d never seen in someone’s face before: pure, unadulterated, unprovoked affection. This step would be taken with his new friend, his _only_ friend for now. His friend that may or may not turn into something more.

 

Dean whispered the words before his brain had even decided,

 

“Yes, I’m agreeing to your deal.”

 

Sam’s face broke into a wide grin and he scooped Dean in for another kiss, burying his fingers in Dean’s short hair and lifting him straight off the floor for a moment. When he pulled away, he was still smiling as wide, his entire face a burning red. “I’m getting rid of these pills, then you’re gonna get your money’s worth, deal?”

 

“What’s that mean?”

 

Sam’s grin turned mischievous. “Guess you’ll have to wait and see. Go lay in bed.”

 

“Sam, I don’t want sex from you. Not yet at least, I—“

 

“Just.. Go lay in bed, Dean.” Sam stroked his cheek for a moment before turning and disappearing into the bathroom with the boxers and pills.

 

When he returned, Dean was stretched out in the bed, gripping the covers to his chest like a life preserver. Sam crawled into the bed – now clad in only Dean’s borrowed boxers – and pulled Dean over to him.

 

“You wanted someone to hang with, and someone to sleep with. I’m gonna give you the best cuddling you’ve ever had, got it?”

 

Dean looked at Sam for a long moment before nodding, letting Sam pull him until he was pressed tight to Sam’s body, his chest to Dean’s back.

 

They laid in a comfortable silence, Sam’s big arm curled almost protectively around Dean’s middle.

 

Dean lay silently, staring into the dark of his room. For the first time in his life, however, Dean realized that the dark unknown didn’t seem too dark after all.


End file.
